Jenna Bush Hager has an engagement story for the books. Less than a year before they tied the knot in a “spectacular” Texas wedding, Henry Hager proposed to the TODAY anchor in an idyllic setting. But before he could even pop the question officially in 2007, Jenna had beat him to the punch.

After three months of dating, Jenna revealed during a February 2020 episode of TODAY with Hoda & Jenna that she proposed to her then-boyfriend after a cocktail. “I asked Henry to marry me,” she shared. “He said no, and then he asked me five years later … I might’ve had a Christmas cocktail and we were dancing, and I said, ‘This is it, I know it, let’s just get married, what are we waiting for?’ He smiled, and he was like, ‘I’m crazy about you, but you’re young.’”

Years later, he did propose and the happy couple exchanged vows in 2008. Since then, they’ve welcomed three children together: daughters Poppy and Mila, and son Hal.

In this handout image provided by the White House, Henry and Jenna Hager pose for photographs along the lake at Prairie Chapel Ranch following their wedding ceremony May 10, 2008 near Crawford, Texas. Photo: Shealah Craighead/The White House via Getty Images

But how did their journey to husband and wife begin? Read on to find out how Henry proposed almost two decades ago, see the engagement photo the White House released at the time, and more.

How did Henry Hager propose to Jenna Bush?

On August 15, 2007, Henry Hager popped the question on top of a mountain in Maine.

“I got proposed at [the] top of a mountain,” Jenna shared with her former co-host Hoda Kotb on TODAY in October 2024. “We hiked Cadillac Mountain, which is in Acadia in Maine, a national park, which is so pretty. And he proposed to me at the top.”

Jenna shared that Henry’s proposal caught her by surprise — and she wasn’t in the best mood ahead of time. “I wasn’t predicting it. In fact, I was acting very cranky, a little grumpy,” she recalled. “And he said, ‘Let’s stop for a LUNA bar, the sun is about to come up, let’s watch it together.’ And I said, ‘No, I’m too cold to stop.’ I said, ‘Let’s please keep going.’”

After some back and forth about whether or not they could take a break, Henry eventually got down on one knee and proposed. “And I said yes,” she said. “Then I wasn’t cranky.”

While the proposal was certainly very intimate, there was one person who knew the exciting news before anyone else. “It was private except there was a secret service man a couple paces behind me,” Jenna added, calling that detail about their engagement story “very weird.”

One day later, the White House announced the news to the rest of the world with a short statement and photo (below) of the happy couple. “President and Mrs. George W. Bush are happy to announce the engagement of their daughter, Jenna Bush, to Mr. Henry Hager, son of the Honorable and Mrs. John H. Hager of Richmond, Virginia,” the statement read.

In this handout photo provided by the White House, Jenna Bush and Mr. Henry Hager pose for a photograph on May 6, 2006. Photo: Kimberlee Hewitt/White House via Getty Images

Henry Hager asked President George W. Bush for his permission to propose

More than a month before he proposed, Henry had gotten President George W. Bush’s blessing to do so. Jenna revealed in 2023 on TODAY that Henry was able to secure some time on the president’s schedule over the Fourth of July weekend in 2007 at Camp David.

“I was like, ‘Come see the movie,’ or ‘We’re going to go do this,’” she recalled. “We had friends there, and he was like, ‘No.’ He called my dad. He’s like, ‘I’d like to come speak to you.’ He’s like ‘I’m taking a nap. Come in a couple hours.’ So [Henry] had to sit and stew.”

Henry Hager and Jenna Bush-Hager attend the Russell Simmons Diamond Empowerment Fund – Dallas Rocks Benefit Dinner on November 14, 2009 in Dallas, Texas. Photo: Johnny Nunez/WireImage

When Henry finally had a chance to speak with President Bush, Jenna said he had a “seven-point plan of why he wanted to marry me and how he was going to take care of me.”

“My dad goes, ‘Henry, I said yes. You don’t need to go through anything else. Laura, Henry’s proposing,’ and that was that,” Jenna shared. “Good thing he did it.”